TWI509056B - Liquid crystal compositon and liquid crystal display divice - Google Patents

Description

Liquid crystal composition and liquid crystal display element

The present invention mainly relates to a liquid crystal composition suitable for an AM (active matrix) device or the like, an AM device including the composition, and the like. In particular, there is a liquid crystal composition having a negative dielectric anisotropy, and an IPS (in-plane switching) mode, a VA (vertical alignment) mode, or a PSA (polymer) containing the composition. Sustain alignment, a component of the polymer stable alignment mode.

In the liquid crystal display device, the classification of the operating mode based on the liquid crystal is PC (phase change), TN (twisted nematic), STN (super twisted nematic), ECB. (electrically controlled birefringence), OCB (optically compensated bend), IPS (in-plane switching), VA (vertical alignment), PSA (polymer sustained alignment, Polymer stable alignment mode and the like. The component-based driving methods are classified into PM (passive matrix) and AM (active matrix). The PM can be classified into a static type, a multiplex type, etc., and the AM can be classified into a TFT (thin film transistor), a MIM (metal insulator metal), and the like. The TFTs are classified into amorphous silicon and polycrystalline silicon. Polycrystalline germanium is classified into a high temperature type and a low temperature type according to the manufacturing steps. The classification based on the light source is a reflection type using natural light, a penetration type using a backlight, and a semi-transmissive type using both natural light and a backlight.

These elements contain a liquid crystal composition having suitable characteristics. The liquid crystal composition has a nematic phase. In order to obtain an AM element having good general characteristics, the general characteristics of the composition are improved. The association of the general characteristics of the two is summarized in Table 1 below. The general characteristics of the composition are further described based on commercially available AM components. The temperature range of the nematic phase is related to the temperature range over which the component can be used. The preferred upper limit temperature of the nematic phase is about 70 ° C or higher, and the preferred lower limit temperature of the nematic phase is about -10 ° C or lower. The viscosity of the composition is related to the response time of the component. In order to display a moving image with a component, it is preferable that the response time is short. Therefore, it is preferred that the viscosity of the composition is small. More preferably, the viscosity is low at lower temperatures.

The optical anisotropy of the composition is related to the contrast of the component. The product (Δn × d) of the optical anisotropy (Δn) of the composition and the cell gap (d) of the device is designed to maximize the contrast. Appropriate value-added In the type of operating mode. It is in the range of about 0.30 μm to about 0.40 μm in the VA mode element and about 0.20 μm to about 0.30 μm in the IPS mode element. In this case, a composition having a large optical anisotropy in an element having a small cell gap is preferable. The dielectric anisotropy with a large absolute value of the composition contributes to a low threshold voltage of the element, a small power consumption, and a large contrast ratio. Therefore, a dielectric anisotropy having a large absolute value is preferred. The large specific resistance of the composition contributes to the large voltage holding ratio of the element and the large contrast. Therefore, it is preferred to have a composition having a large specific resistance not only at room temperature but also at a high temperature in the initial stage. A composition having a large specific resistance not only at room temperature but also at a high temperature after long-term use is preferred. The stability of the composition for ultraviolet light and heat is related to the life of the liquid crystal display element. When the stability is high, the life of the component is long. Such characteristics are preferable for AM elements used in liquid crystal projectors, liquid crystal televisions, and the like.

In an AM device having a TN mode, a composition having positive dielectric anisotropy is used. On the other hand, in the AM device having the VA mode, a composition having a negative dielectric anisotropy is used. In an AM device having an IPS mode, a composition having positive or negative dielectric anisotropy is used. In an AM device having a PSA mode, a composition having positive or negative dielectric anisotropy is used. Examples of the liquid crystal composition having a negative dielectric anisotropy are disclosed in Patent Documents 1 to 7 as described below.

[Previous Technical Literature]

[Patent Literature]

[Patent Document 1] International Publication No. 2009/034867

[Patent Document 2] Japanese Patent Laid-Open Publication No. 2009-035630

[Patent Document 3] Japanese Patent Laid-Open Publication No. 2008-088164

[Patent Document 4] Japanese Patent Laid-Open Publication No. 2008-038109

[Patent Document 5] International Publication No. 2007/108307

[Patent Document 6] International Publication No. 2007/077872

[Patent Document 7] Japanese Patent Laid-Open Publication No. 2000-053602

The ideal AM device has a wide temperature range, short response time, high contrast ratio, low threshold voltage, large voltage holding ratio, and long life. Ideally, the response time is shorter than 1 millisecond. Therefore, the ideal characteristics of the composition are that the upper limit temperature of the nematic phase is high, the lower limit temperature of the nematic phase is low, the viscosity is small, the optical anisotropy is appropriate, the positive or negative dielectric anisotropy is large, the specific resistance is large, and ultraviolet rays are applied. High stability and high thermal stability.

An object of the present invention is that the upper limit temperature of the nematic phase is high, the lower limit temperature of the nematic phase is low, the viscosity is small, the optical anisotropy is appropriate, the negative dielectric anisotropy is large, the specific resistance is large, and the ultraviolet ray stability is high. A liquid crystal composition that satisfies at least one of characteristics of high thermal stability characteristics. Other objects are liquid crystal compositions having an appropriate balance between at least two characteristics, particularly liquid crystal compositions which sufficiently satisfy optical anisotropy and large negative dielectric anisotropy. Other objects are liquid crystal display elements containing such a composition. Other objects are compositions having appropriate optical anisotropy (large optical anisotropy or large optical anisotropy), large negative dielectric anisotropy, high UV stability, and short response time and voltage retention. AM components with large, high contrast, long life and other characteristics.

A liquid crystal composition containing at least one compound selected from the group consisting of compounds represented by formula (1) as a first component, and a liquid crystal display element containing the composition, and a second component At least one compound selected from the group consisting of compounds represented by formula (2), the ratio of the first component is in the range of 5 wt% to 95 wt%, based on the total weight of the liquid crystal composition, and has a negative dielectric anisotropy Sex.

Here, R ¹ , R ² , R ³ and R ^{4 are each} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyloxy group having 2 to 12 carbon atoms, and a carbon number. An alkenyl group having 2 to 12 alkenyl groups or an arbitrary hydrogen substituted by fluorine having 2 to 12 carbon atoms;

X ¹ , X ² and X ^{3 are} independently hydrogen, fluorine or chlorine; Z ^{1 is} independently a single bond, ethyl, methyleneoxy or carbonyloxy; m is 1, 2 or 3; Wherein, when X ¹ is hydrogen, X ² and X ³ are fluorine or chlorine; and in formula (2), at least one Z ¹ is a methyleneoxy group or at least one ring A is

[Effects of the Invention]

The invention has the advantages that the upper limit temperature of the nematic phase is high, the lower limit temperature of the nematic phase is low, the viscosity is small, the optical anisotropy is appropriate, the negative dielectric anisotropy is large, the specific resistance is large, and the ultraviolet ray stability is high, A liquid crystal composition that satisfies at least one characteristic among high thermal stability characteristics. One aspect of the invention is a liquid crystal composition having an appropriate balance between at least two characteristics. Other aspects are liquid crystal display elements containing such a composition. Other aspects are compositions having suitable optical anisotropy, large negative dielectric anisotropy, high UV stability, and AM components having short response time, high voltage holding ratio, large contrast, and long life. .

The above and other objects, features and advantages of the present invention will become more <RTIgt;

The usage of the terms in this specification is as follows. The liquid crystal composition of the present invention or the liquid crystal display element of the present invention may be simply referred to as "composition" or "element", respectively. The liquid crystal display element is a general term for a liquid crystal display panel and a liquid crystal display module. The "liquid crystal compound" means a compound having a nematic phase or a smectic liquid crystal phase, or a compound which can be used as a component of a composition although it does not have a liquid crystal phase. Such a compound has, for example, a six-membered ring such as 1,4-cyclohexylene or 1,4-phenylene, and has a rod-like molecular structure. An optically active compound and a polymerizable compound are sometimes added to the composition. These compounds are classified as additives even if they are liquid crystal compounds. At least one compound selected from the group consisting of the compounds represented by the formula (1) is sometimes simply referred to as "compound (1)". The "compound (1)" represents one compound represented by the formula (1) or two or more compounds. The same applies to the compounds represented by other formulas. "Arbitrary" not only indicates that the position is arbitrary but also indicates that the number is arbitrary, but does not include the case where the number is zero.

The upper limit temperature of the nematic phase is sometimes simply referred to as "upper limit temperature". The lower limit temperature of the nematic phase is sometimes simply referred to as "lower limit temperature". "Greater specific resistance" means that the composition has a large specific resistance at the initial stage not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase, and is not only at room temperature but also close to the nematic after long-term use. The temperature of the upper limit temperature also has a large specific resistance. "High voltage holding ratio" means that the element has a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase in the initial stage, and is not only at room temperature but also close to the direction after long-term use. The temperature of the upper limit temperature of the column also has a large voltage holding ratio. When the characteristics such as optical anisotropy are described, the value obtained by the method described in the examples is used. The first component is a compound or a compound of two or more. The "ratio of the first component" is expressed by the weight percentage (wt%) of the first component based on the total weight of the liquid crystal composition. The same applies to the ratio of the second component and the like. The proportion of the additive to be mixed in the composition is expressed by weight percentage (wt%) or weight parts per million (ppm) based on the total weight of the liquid crystal composition.

In the chemical formula of the component compound, the symbol of R ¹ is used in a plurality of compounds. Among the two compounds of any of these, the selected R ¹ may be the same or different. For example, the compound (1) of R ¹ is ethyl, the compound (1-1) wherein R ¹ is an example of an ethyl. Also the presence of the compound (1) of R ¹ is ethyl, the compound (1-1) wherein R ¹ is an example of the propyl group. This rule also applies to R ² , Z ^{1 ,} etc.

The present invention is as follows.

A liquid crystal composition having a negative dielectric anisotropy and containing, as a first component, at least one compound selected from the group consisting of compounds represented by formula (1), and as a second component At least one compound selected from the group consisting of compounds represented by formula (2), the ratio of the first component is in the range of 5 wt% to 95 wt% based on the total weight of the liquid crystal composition.

Here, R ¹ , R ² , R ³ and R ^{4 are each} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyloxy group having 2 to 12 carbon atoms, and a carbon number. An alkenyl group having 2 to 12 alkenyl groups or an arbitrary hydrogen substituted by fluorine having 2 to 12 carbon atoms;

X ¹ , X ² and X ^{3 are} independently hydrogen, fluorine or chlorine; Z ^{1 is} independently a single bond, ethyl, methyleneoxy or carbonyloxy; m is 1, 2 or 3; Wherein, when X ¹ is hydrogen, X ² and X ³ are fluorine or chlorine; and in formula (2), at least one Z ¹ is a methyleneoxy group or at least one ring A is

2. The liquid crystal composition according to Item 1, wherein the first component is at least one compound selected from the group consisting of compounds represented by formula (1-1) and formula (1-2).

Here, R ¹ and R ^{2 are} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyloxy group having 2 to 12 carbon atoms, and an alkenyl group having 2 to 12 carbon atoms. The base or any hydrogen which is substituted by fluorine is an alkenyl group having 2 to 12 carbon atoms.

3. The liquid crystal composition according to Item 2, wherein the first component is at least one compound selected from the group consisting of compounds represented by formula (1-1).

4. The liquid crystal composition according to any one of the items 1 to 3, wherein the second component is selected from the group consisting of compounds represented by formula (2-1) to formula (2-10). At least one compound,

Here, R ³ and R ^{4 are} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyloxy group having 2 to 12 carbon atoms, and an alkenyl group having 2 to 12 carbon atoms. The base or any hydrogen which is substituted by fluorine is an alkenyl group having 2 to 12 carbon atoms.

5. The liquid crystal composition according to Item 4, wherein the second component is at least one compound selected from the group consisting of compounds represented by formula (2-5).

6. The liquid crystal composition according to Item 4, wherein the second component is at least one compound selected from the group consisting of compounds represented by formula (2-7).

The liquid crystal composition according to any one of the items 1 to 6, wherein the ratio of the first component is in the range of 10 wt% to 60 wt% based on the total weight of the liquid crystal composition, and the second The ratio of the components is in the range of 10 wt% to 90 wt%.

The liquid crystal composition according to any one of the items 1 to 7, further comprising at least one compound selected from the group consisting of compounds represented by formula (3) as a third component,

Here, R ⁵ and R ^{6 are} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or a carbon in which any hydrogen is replaced by fluorine. The number is 2 to 12 alkenyl; ring B, ring C and ring D are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or 3- Fluoro-1,4-phenylene; Z ² and Z ^{3 are} independently a single bond, an extended ethyl group, a methyleneoxy group, or a carbonyloxy group; p is 0, 1 or 2; when p is 1, the ring B, ring C and ring D are independently 1,4-cyclohexylene or 1,4-phenylene.

9. The liquid crystal composition according to Item 8, wherein the third component is at least one compound selected from the group consisting of compounds represented by formula (3-1) to formula (3-11),

Here, R ⁵ and R ^{6 are} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or a carbon in which any hydrogen is replaced by fluorine. The number is 2 to 12 alkenyl groups.

10. The liquid crystal composition according to Item 9, wherein the third component is at least one compound selected from the group consisting of compounds represented by formula (3-1).

11. The liquid crystal composition according to Item 9, wherein, in the formula (3-1), R ⁵ is an alkyl group having 1 to 12 carbon atoms, and R ⁶ is an alkenyl group having 1 to 12 carbon atoms.

12. The liquid crystal composition according to Item 9, wherein, in the formula (3-1), R ⁵ and R ⁶ are each an alkyl group having 1 to 12 carbon atoms.

13. The liquid crystal composition according to Item 9, wherein the third component is at least one compound selected from the group consisting of compounds represented by formula (3-1), and is selected from the group consisting of formula (3-4) A mixture of at least one compound of the group of compounds.

14. The liquid crystal composition according to Item 9, wherein the third component is at least one compound selected from the group consisting of compounds represented by formula (3-9).

The liquid crystal composition according to any one of items 8 to 14, wherein the ratio of the third component is in the range of 5 wt% to 60 wt% based on the total weight of the liquid crystal composition.

The liquid crystal composition according to any one of the items 1 to 5, further comprising a group selected from the group consisting of compounds represented by formula (4-1) and formula (4-2) as a fourth component Group of at least one compound,

Here, R ⁷ and R ^{8 are} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or a carbon in which any hydrogen is replaced by fluorine. The number is 2 to 12 alkenyl; ring E, ring F and ring G are independently 1,4-cyclohexylene or 1,4-phenyl; Z ⁴ is a single bond, an extended ethyl group, or a carbonyloxy group; Z ⁵ and Z ^{6 are} independently a single bond, an extended ethyl group, a methyleneoxy group, or a carbonyloxy group; X ⁴ and X ⁵ are fluorine or chlorine; Y ¹ is hydrogen or a methyl group; q is 1, 2 or 3 ;r and s are independently 0, 1, 2 or 3, and the sum of r and s is 3 or less.

17. The liquid crystal composition according to Item 16, wherein the fourth component is selected from the group consisting of Formula (4-1-1) to Formula (4-1-9), and Formula (4-2-1). (4-2-5) at least one compound of the group of compounds represented,

Here, R ⁷ and R ^{8 are} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or a carbon in which any hydrogen is replaced by fluorine. The number is 2 to 12 alkenyl groups.

18. The liquid crystal composition according to Item 17, wherein the fourth component is at least one compound selected from the group consisting of compounds represented by formula (4-1-1).

19. The liquid crystal composition according to Item 17, wherein the fourth component is at least one compound selected from the group consisting of compounds represented by formula (4-1-3).

Item 20. The liquid crystal composition according to Item 17, wherein the fourth component is at least one compound selected from the group consisting of compounds represented by formula (4-1-2), and is selected from the group consisting of formula (4-1-). 5) At least one compound of the group of compounds indicated.

The liquid crystal composition according to item 17, wherein the fourth component is at least one compound selected from the group consisting of compounds represented by formula (4-2-4).

The liquid crystal composition according to any one of items 16 to 21, wherein the ratio of the fourth component is in the range of 5 wt% to 50 wt% based on the total weight of the liquid crystal composition.

The liquid crystal composition according to any one of the items 1 to 22, wherein the upper limit temperature of the nematic phase is 70 ° C or higher, and the optical anisotropy (25 ° C) at a wavelength of 589 nm is 0.08 or more. And the dielectric anisotropy (25 ° C) at a frequency of 1 kHz is -2 or less.

A liquid crystal display element comprising the liquid crystal composition according to any one of items 1 to 23.

The liquid crystal display device of claim 24, wherein the operation mode of the liquid crystal display element is VA mode, IPS mode, or PSA mode, and the driving mode of the liquid crystal display element is an active matrix mode.

The invention also includes the following items. 1) the composition further containing the optically active compound, and 2) the composition further containing an additive such as an antioxidant, an ultraviolet absorber, or an antifoaming agent. 3) an AM device containing the composition, 4) an element having the composition and having a mode of TN, ECB, OCB, IPS, VA or PSA, 5) a penetrating element containing the composition, 6) Use of the composition as a composition having a nematic phase, and 7) use as an optically active composition by adding an optically active compound to the composition.

The composition of the present invention will be described in the following order. First, the constitution of the component compounds in the composition will be described. Second, the main characteristics of the component compound and the main effects of the compound on the composition will be explained. Third, the composition of the components in the composition, the preferred ratio of the components, and the basis thereof. Fourth, a preferred form of the component compound will be described. Fifth, a specific example of the component compound is shown. Sixth, an additive which can be mixed in the composition will be described. Seventh, a method for synthesizing a component compound will be described. Finally, the use of the composition is explained.

First, the constitution of the component compounds in the composition will be described. The composition of the present invention can be classified into composition A and composition B. The composition A may further contain other liquid crystal compounds, additives, impurities, and the like. The "other liquid crystal compound" is a liquid crystal compound different from the compound (1), the compound (2), the compound (3), the compound (4-1), and the compound (4-2). Such compounds are mixed in the composition for the purpose of further adjusting the properties. Among other liquid crystal compounds, it is preferred that the cyano compound is less from the viewpoint of stability against heat or ultraviolet rays. A more preferable ratio of the cyano compound is 0 wt%. The additive is an optically active compound, an antioxidant, a UV absorber, a pigment, an antifoaming agent, a polymerizable compound, a polymerization initiator, and the like. The impurity is a compound or the like mixed in the step of synthesizing a component compound or the like. This compound is classified as an impurity here even if it is a liquid crystalline compound.

The composition B consists essentially only of a compound selected from the group consisting of the compound (1), the compound (2), the compound (3), the compound (4-1), and the compound (4-2). "Substantially" means that the composition does not contain a liquid crystal compound different from the compounds except for additives and impurities. Composition B has a smaller number of components than composition A. From the viewpoint of cost reduction, the composition B is better than the composition A. The composition A is more preferable than the composition B from the viewpoint of further adjusting the physical properties by mixing other liquid crystal compounds.

Second, the main characteristics of the component compound and the main effects of the compound on the properties of the composition are explained. The main characteristics of the component compounds are summarized in Table 2 based on the effects of the present invention. In the symbols of Table 2, L indicates large or high, M indicates moderate, and S indicates small or low. The notation L, M, S is a classification based on a qualitative comparison between the constituent compounds, and 0 (zero) indicates that the value is substantially zero.

When the component compounds are mixed in the composition, the main effects of the component compounds on the properties of the composition are as follows. Compound (1) increases optical anisotropy and lowers viscosity. Compound (2) increases the absolute value of dielectric anisotropy. The compound (3) lowers the viscosity, adjusts the appropriate optical anisotropy, raises the upper limit temperature, and lowers the lower limit temperature. The compound (4-1) and the compound (4-2) increase the absolute value of the dielectric anisotropy and lower the lower limit temperature.

Third, the composition of the components in the composition, the preferred ratio of the components, and the basis thereof. The combination of the components in the composition is a first component + a second component, a first component + a second component + a third component, a first component + a second component + a fourth component, and a first component + a second component + Three components + fourth component.

In order to increase the absolute value of the dielectric anisotropy, a preferred combination of components in the composition is the first component + the second component; in order to lower the viscosity or to increase the upper limit temperature, a preferred combination of components in the composition is first Component + second component + third component; and in order to further increase the absolute value of dielectric anisotropy or to increase the upper limit temperature, a preferred combination of components in the composition is first component + second component + third component + The fourth component.

In order to increase the absolute value of the optical anisotropy, a preferred ratio of the first component is about 10% by weight or more; and in order to lower the minimum temperature, a preferred ratio of the first component is about 60% by weight or less. A more desirable ratio is in the range of about 10 wt% to 55 wt%. A particularly preferred ratio is in the range of from about 15% by weight to about 50% by weight.

In order to increase the absolute value of the dielectric anisotropy, a preferred ratio of the second component is about 10% by weight or more; and in order to lower the minimum temperature, a preferred ratio of the second component is about 90% by weight or less. More preferably, the ratio is from about 20% by weight to about 70% by weight in order to lower the viscosity. A particularly preferred ratio is in the range of from about 35 wt% to about 65 wt%.

In order to lower the viscosity, a preferred ratio of the third component is about 5% by weight or more; in order to increase the absolute value of the dielectric anisotropy, a preferred ratio of the third component is about 60% by weight or less. A more desirable ratio is in the range of about 10 wt% to 50 wt%. A particularly preferred ratio is in the range of from about 15% by weight to about 40% by weight.

In order to increase the absolute value of the dielectric anisotropy, a preferred ratio of the fourth component is about 5 wt% or more; and in order to lower the lower limit temperature, a preferred ratio of the fourth component is about 50 wt% or less. More preferably, the ratio is in the range of from about 10% by weight to about 50% by weight. A particularly preferred ratio is in the range of from about 10% by weight to about 30% by weight.

Fourth, a preferred form of the component compound will be described.

R ¹ , R ² , R ³ and R ^{4 are} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyloxy group having 2 to 12 carbon atoms, and a carbon number of 2 to 2. The alkenyl group of 12 or an arbitrary number of carbons substituted with fluorine is an alkenyl group having 2 to 12 carbon atoms. R ⁵ and R ^{6 are} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or a carbon number of 2 in which any hydrogen is replaced by fluorine. Alkenyl ~12. R ⁷ and R ^{8 are} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or a carbon number of 2 in which any hydrogen is replaced by fluorine. Alkenyl ~12.

In order to lower the lower limit temperature and to lower the viscosity, it is preferred that R ¹ , R ² , R ³ , R ⁵ or R ⁷ is an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 2 to 12 carbon atoms. In order to lower the lower limit temperature and to lower the viscosity, it is preferred that R ⁴ , R ⁶ or R ⁸ is an alkyl group having 1 to 12 carbon atoms; and in order to increase the absolute value of dielectric anisotropy, R ⁴ , R ⁶ or R is preferred. ⁸ is an alkoxy group having 1 to 12 carbon atoms. More preferably, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ or R ⁸ is an alkyl group having 1 to 12 carbon atoms for the purpose of improving ultraviolet light or heat stability and the like.

Preferred alkyl groups are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl. More desirable alkyl groups are ethyl, propyl, butyl, pentyl or heptyl for decreasing the viscosity.

Preferred alkoxy groups are methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy or heptyloxy. More preferably, the alkoxy group is a methoxy group or an ethoxy group in order to lower the viscosity.

Preferred alkenyl groups are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3- Pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl. More preferably, the alkenyl group is a vinyl group, a 1-propenyl group, a 3-butenyl group, or a 3-pentenyl group in order to lower the viscosity. The preferred stereo configuration of -CH=CH- in the alkenyl groups depends on the position of the double bond. In order to lower the viscosity and the like, it is considered to be in an alkenyl group such as 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 3-pentenyl or 3-hexenyl. Preferably, it is trans. Among the alkenyl groups such as 2-butenyl, 2-pentenyl and 2-hexenyl, cis is preferred. Among the alkenyl groups, a linear alkenyl group is more preferred than a branched alkenyl group.

Preferred alkenyloxy groups are vinyloxy, allyloxy, 3-butenyloxy, 3-pentenyloxy, or 4-pentenyloxy. In order to lower the viscosity, the alkenyloxy group is more preferably an allyloxy group or a 3-butenyloxy group.

Preferred examples of the alkenyl group in which any hydrogen is substituted by fluorine are 2,2-difluorovinyl, 3,3-difluoro-2-propenyl, 4,4-difluoro-3-butenyl, 5, 5-difluoro-4-pentenyl, and 6,6-difluoro-5-hexenyl. More desirable examples are 2,2-difluorovinyl and 4,4-difluoro-3-butenyl for decreasing the viscosity.

m is 1, 2 or 3. In order to increase the upper limit temperature, m is preferably 2 or 3. p is 0, 1, or 2. In order to increase the upper limit temperature, p is preferably 2; in order to lower the viscosity, p is preferably 0 or 1. q is 1, 2 or 3. In order to increase the upper limit temperature, q is preferably 2 or 3; and in order to lower the viscosity, q is preferably 1. r and s are independently 0, 1, 2 or 3, and the sum of r and s is 3 or less. In order to increase the upper limit temperature, preferably r and s are 2 or 3, respectively, and in order to lower the viscosity, it is preferred that r and s are respectively 1.

Ring A is independent

When at least one Z ^{1 is} not a methyleneoxy group, at least one ring A is

When m is 2 or 3, any two rings A may be the same or different. In order to improve the optical anisotropy, the ring A is preferably a 1,4-phenylene group. In order to improve the dielectric anisotropy, the ring A is preferably

Ring B, Ring C and Ring D are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or 3-fluoro-1,4-phenylene When p is 1, ring B, ring C and ring D are 1,4-cyclohexylene or 1,4-phenylene. When p is 2, two rings B may be the same or different. In order to increase the upper limit temperature or to lower the viscosity, it is preferred that ring B, ring C or ring D is 1,4-cyclohexylene; in order to improve optical anisotropy, ring B, ring C or ring D is preferably 1,4- Stretch phenyl. Ring E, ring F and ring G are independently 1,4-cyclohexylene or 1,4-phenylene. When q is 2 or 3, any two rings E may be the same or different, and when r is 2 or 3 Any two rings F may be the same or different. When s is 2 or 3, any two rings F and G may be the same or different. In order to increase the upper limit temperature or to lower the viscosity, it is preferred that ring E, ring F or ring G is 1,4-cyclohexylene; in order to improve optical anisotropy, it is preferred that ring E, ring F or ring G is 1,4- Stretch phenyl. In order to increase the upper limit temperature, the stereo configuration associated with 1,4-cyclohexylene is more preferred than the cis.

X ¹ , X ² and X ^{3 are} independently hydrogen, fluorine or chlorine, and when X ¹ is hydrogen, X ² and X ³ are fluorine or chlorine. In order to lower the viscosity, it is preferred that X ¹ , X ² or X ³ is hydrogen and fluorine. X ⁴ and X ^{5 are} independently fluorine or chlorine. In order to lower the viscosity, it is preferred that X ⁴ or X ⁵ is fluorine.

Y ¹ is hydrogen or methyl. In order to lower the viscosity, Y ¹ is preferably hydrogen; and in order to improve the stability against ultraviolet rays, heat, etc., Y ¹ is preferably a methyl group.

Z ¹ , Z ² , Z ³ , Z ⁵ and Z ^{6 are} independently a single bond, an extended ethyl group, a methyleneoxy group or a carbonyloxy group, and when m is 2 or 3, any two Z ¹ may be the same or Different, when p is 2, 2 Z ² may be the same or different. When r is 2 or 3, any two Z ⁵ may be the same or different. When s is 2 or 3, any two Z ⁶ may be the same. different. In order to lower the viscosity, it is preferred that Z ¹ , Z ² , Z ³ , Z ⁵ or Z ⁶ is a single bond; in order to improve the dielectric anisotropy, Z ¹ , Z ² , Z ³ , Z ⁵ or Z ⁶ is preferably a sub- Methyloxy. Z ⁴ is a single bond, an extended ethyl group or a carbonyloxy group, and when q is 2 or 3, any two Z ⁴ may be the same or different. In order to lower the viscosity, Z ⁴ is preferably a single bond; and in order to lower the lower limit temperature, Z ⁴ is preferably an exoethyl group.

Fifth, a specific example of the component compound is shown.

In the preferred compounds described below, R ⁷ and R ^{8 are} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or any of them. The number of carbons in which hydrogen is replaced by fluorine is 2 to 12 alkenyl groups. R ⁹ and R ^{10 are} independently a straight-chain alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyloxy group having 2 to 12 carbon atoms, and a straight carbon number of 2 to 12 Alkenyl chain. R ¹¹ and R ^{12 are} independently an alkyl group having a linear alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, and a linear alkenyl group having 2 to 12 carbon atoms.

Desirable compound (1) is the compound (1-1-1) to the compound (1-2-1). More preferably, the compound (1) is the compound (1-1-1). Desirable compound (2) is the compound (2-1-1) to the compound (2-10-1). More preferably, the compound (2) is the compound (2-1-1) and the compound (2-5-1) to the compound (2-10-1). Particularly preferred compound (2) are the compound (2-1-1), the compound (2-5-1), and the compound (2-7-1). Desirable compound (3) is the compound (3-1-1) to the compound (3-11-1). More preferably, the compound (3) is the compound (3-1-1) to the compound (3-4-1), and the compound (3-7-1) to the compound (3-11-1). Particularly preferred compound (3) is the compound (3-1-1), the compound (3-4-1), the compound (3-7-1), the compound (3-9-1), and the compound (3-11-). 1). Desirable compound (4-1) is the compound (4-1-1-1) to the compound (4-1-9-1). More desirable compound (4-1) is the compound (4-1-1-1) and the compound (4-1-5-1). Particularly preferred compound (4-1) is the compound (4-1-1-1) and the compound (4-1-3-1). Desirable compound (4-2) is the compound (4-2-1-1) to the compound (4-2-5-1). Particularly preferred compound (4-2) is the compound (4-2-4-1).

Sixth, an additive which can be mixed in the composition will be described. Such additives are optically active compounds, antioxidants, ultraviolet absorbers, pigments, antifoaming agents, polymerizable compounds, polymerization initiators, and the like. In order to induce a twist angle of the liquid crystal, an optically active compound is mixed in the composition. Examples of such a compound are the compound (5-1) to the compound (5-4). A preferred ratio of the optically active compound is 5% by weight or less. More preferably, the ratio is in the range of from about 0.01% by weight to about 2% by weight.

In order to prevent a decrease in specific resistance due to heating in the atmosphere or to maintain a large voltage holding ratio even at a temperature close to the upper limit temperature of the nematic phase even after using the element for a long period of time, The antioxidant is mixed.

A preferred example of the antioxidant is a compound (6) wherein w is an integer of from 1 to 9. In the compound (6), w is preferably 1, 3, 5, 7 or 9. More preferably, w is 1 or 7. The compound (6) having w of 1 has a large volatility, and therefore is effective in preventing a decrease in specific resistance due to heating in the atmosphere. The compound of w (7) has a small volatility and is therefore effective in maintaining a large voltage retention not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase, even after long-term use of the element. rate. In order to obtain this effect, a preferred ratio of the antioxidant is about 50 ppm or more; in order not to lower the upper limit temperature or to increase the lower limit temperature, the preferred ratio of the antioxidant is 600 ppm or less. A more desirable ratio is in the range of about 100 ppm to 300 ppm.

Preferred examples of the ultraviolet absorber are a benzophenone derivative, a benzoate derivative, a triazole derivative and the like. Light stabilizers such as amines having steric hindrance are also preferred. In order to obtain this effect, a preferred ratio of the adsorbents or stabilizers is about 50 ppm or more; in order not to lower the upper limit temperature or to increase the lower limit temperature, a preferred ratio of the adsorbents or stabilizers is about 10,000 ppm or less. . A more desirable ratio is in the range of from about 100 ppm to about 10,000 ppm.

In order to be suitable for the element of the guest host (GH) mode, a dichroic dye such as an azo dye or an anthraquinone dye is mixed in the composition. A preferred ratio of pigment is in the range of from about 0.01% by weight to about 10% by weight. In order to prevent foaming, an antifoaming agent such as dimethyl silicone oil or methylphenyl sulfonate is mixed in the composition. In order to obtain this effect, a preferred ratio of the antifoaming agent is about 1 ppm or more; in order to prevent display failure, a preferable ratio of the antifoaming agent is 1000 ppm or less. A more desirable ratio is in the range of from about 1 ppm to about 500 ppm.

In order to be suitable for a polymer sustained alignment (PSA) mode element, a polymerizable compound is mixed in the composition. Preferred examples of the polymerizable compound are those having an acrylate, a methacrylate, a vinyl group, a vinyloxy group, a propenyl ether, an epoxy group (ethylene oxide, propylene oxide), a vinyl ketone or the like. a compound based on it. A particularly preferred example is a derivative of acrylate or methacrylate. In order to obtain this effect, a preferred ratio of the polymerizable compound is about 0.05% by weight or more; in order to prevent display defects, a preferable ratio of the polymerizable compound is about 10% by weight or less. A more desirable ratio is in the range of about 0.1 wt% to 2 wt%. The polymerizable compound is preferably polymerized by UV irradiation or the like in the presence of a suitable initiator such as a photopolymerization initiator. Suitable conditions for the polymerization, suitable types of initiators, and suitable amounts are known to those skilled in the art and are described in the literature. For example, Irgacure 651 (registered trademark), Irgacure 184 (registered trademark) or Darocure 1173 (registered trademark) (Ciba Japan K.K.), which is a photopolymerization initiator, is suitable for radical polymerization. A preferred ratio of the photopolymerization initiator is in the range of from about 0.1% by weight to about 5% by weight of the polymerizable compound, and particularly preferably in the range of from about 1% by weight to about 3% by weight.

Seventh, a method for synthesizing a component compound will be described. These compounds can be synthesized by a known method. The synthesis method is exemplified. The compound (1-1-1) can be synthesized by the method disclosed in Japanese Patent Laid-Open Publication No. 2006-503130. The compound (2-5-1) can be synthesized by the method disclosed in Japanese Laid-Open Patent Publication No. 2000-008040. The compound (3-1-1) can be synthesized by the method disclosed in Japanese Laid-Open Patent Publication No. SHO 59-176221. The compound (4-1-1-1) can be synthesized by the method described in JP-A-2-503441. Antioxidants are commercially available. A compound of formula (6) wherein w is 1 is available from Aldrich Corporation (Sigma-Aldrich Corporation). The compound (6) wherein w is 7 can be synthesized by the method described in the specification of U.S. Patent No. 3,660,505.

Compounds not described for synthesis can be synthesized by organic synthesis (Organic Syntheses, John Wiley & Sons, Inc.), Organic Reactions (Organic Reactions, John Wiley & Sons, Inc), Comprehensive Organic Synthesis (Pergamon Press), New It is synthesized by the method described in the book of Experimental Chemistry (Maruzen). The composition can be prepared by a known method from the compound thus obtained. For example, the component compounds are mixed and then dissolved by heating to each other.

Finally, the use of the composition is explained. Most of the compositions have a lower limit temperature of about -10 ° C or lower, an upper limit temperature of about 70 ° C or higher, and an optical anisotropy in the range of about 0.07 to about 0.20. The component containing the composition has a large voltage holding ratio. This composition is suitable for an AM element. This composition is particularly suitable for a penetrating AM element. The composition having an optical anisotropy in the range of about 0.08 to about 0.25 can be prepared by controlling the ratio of the component compounds or by mixing other liquid crystal compounds. This composition can be used as a composition having a nematic phase, and is used as an optically active composition by adding an optically active compound.

This composition can be used in an AM device. It can also be used in PM components. The composition can be used in an AM device and a PM device having modes such as PC, TN, STN, ECB, OCB, IPS, VA, PSA, and the like. It is particularly preferable to use it in an AM device having an IPS or VA mode. The elements can be reflective, penetrating or semi-transmissive. It is preferably used in a transmissive element. It can also be used in an amorphous germanium-TFT element or a polysilicon-TFT element. It can also be used in a NCAP (nematic curvilinear aligned phase) type element produced by microencapsulating the composition, or a PD (polymer dispersed) type element in which a three-dimensional network polymer is formed in the composition.

[Example]

In order to evaluate the compound contained in the composition and the composition, the composition and the compound were used as measurement targets. When the measurement target is a composition, the measurement is directly performed, and the obtained value is described. When the measurement target compound is a compound, a sample for measurement is prepared by mixing the compound (15 wt%) in a mother liquid crystal (85 wt%). From the value obtained by the measurement, the characteristic value of the compound was calculated by extrapolation. (Extrapolation value) = {(measured value of measurement sample) - 0.85 × (measured value of mother liquid crystal)} / 0.15. At this ratio, when the smectic phase (or crystallization) is precipitated at 25 ° C, the ratio of the compound to the mother liquid crystal is sequentially changed to 10 wt%: 90 wt%, 5 wt%: 95 wt%, 1 wt%: 99 Wt%. The value of the upper limit temperature, optical anisotropy, viscosity, and dielectric anisotropy associated with the compound was determined by the extrapolation method.

The composition of the mother liquid crystal is as follows.

The physical properties were measured in accordance with the methods described below. Most of these measurement methods are those described in the Standard of Electric Industries Association of Japan EIAJ‧ED-2521A or modified.

The upper limit temperature of the nematic phase (NI; ° C): A sample was placed on a hot plate of a melting point measuring apparatus having a polarizing microscope, and heated at a rate of 1 ° C/min. The temperature at which a portion of the sample changes from the nematic phase to the isotropic liquid is measured. The upper limit temperature of the nematic phase is sometimes simply referred to as "upper limit temperature".

Lower limit temperature of the nematic phase (T _C ; ° C): a refrigerator having a nematic phase into a glass vial at 0 ° C, -10 ° C, -20 ° C, -30 ° C, and -40 ° C After storage for 10 days, the liquid crystal phase was observed. For example, when the sample is a nematic phase at -20 ° C and changes to a crystal or a smectic phase at -30 ° C, T _{C is} described as ≦-20 ° C. The lower limit temperature of the nematic phase is sometimes simply referred to as "lower limit temperature".

Viscosity (integral viscosity; η; measured at 20 ° C; mPa ‧ s): E-type rotational viscometer was used in the measurement.

Optical anisotropy (refractive index anisotropy; Δn; measured at 25 ° C): Measurement was carried out by using an Abbe refractometer equipped with a polarizing plate on an eyepiece using light having a wavelength of 589 nm. After rubbing the surface of the main crucible in one direction, the sample is dropped onto the main crucible. The refractive index n∥ was measured when the polarizing direction was parallel to the rubbing direction. The refractive index n⊥ was measured when the direction of polarization was perpendicular to the direction of rubbing. The value of optical anisotropy is calculated from the formula of Δn = n ∥ - n 。 .

Dielectric anisotropy (Δε; measured at 25 ° C): The value of dielectric anisotropy was calculated from the formula Δε = ε ∥ - ε 。 . The dielectric constants (ε∥ and ε⊥) were measured in the following manner.

1) Measurement of dielectric constant (ε∥): A solution of octadecyltriethoxydecane (0.16 mL) in ethanol (20 mL) was applied to a well-washed glass substrate. After the glass substrate was rotated by a spinner, it was heated at 150 ° C for 1 hour. A sample was placed in a VA element having a spacing (cell gap) of 2 glass substrates of 4 μm, and the element was sealed with an adhesive which was hardened by ultraviolet rays. A sine wave (0.5 V, 1 kHz) was applied to the device, and the dielectric constant (ε∥) of the long-axis direction of the liquid crystal molecules was measured after 2 seconds.

2) Measurement of dielectric constant (ε⊥): A polyimide solution was coated on a sufficiently cleaned glass substrate. After the glass substrate was fired, the obtained alignment film was subjected to a rubbing treatment. A sample was placed in a TN device in which the distance between the two glass substrates (cell gap) was 9 μm and the twist angle was 80 degrees. A sine wave (0.5 V, 1 kHz) was applied to the device, and the dielectric constant (ε⊥) of the short-axis direction of the liquid crystal molecules was measured after 2 seconds.

Threshold voltage (Vth; measured at 25 ° C; V): The LCD5100 type luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for measurement. The light source is a halogen lamp. The sample is placed in a normally black mode VA device in which the distance between the two glass substrates (cell gap) is 4 μm, and the rubbing direction is anti-parallel, and the adhesive is cured by ultraviolet rays. element. The voltage applied to the element (60 Hz, rectangular wave) was increased stepwise from 0 V to 0.02 V each time to 20 V. At this time, the element was irradiated with light from the vertical direction, and the amount of light passing through the element was measured. A voltage-transmission curve having a transmittance of 100% when the amount of light is maximum and a transmittance of 0% when the amount of light is minimum is prepared. The threshold voltage is the voltage at which the transmittance becomes 10%.

Voltage holding ratio (VHR-1; 25 ° C; %): The TN device used for the measurement had a polyimide film, and the interval (cell gap) between the two glass substrates was 5 μm. The element is sealed after being placed in the sample as an adhesive which can be polymerized by ultraviolet light. A pulse voltage (5 V, 60 microseconds) was applied to the TN device to charge. The voltage of the attenuation was measured with a high-speed voltmeter between 16.7 msec, and the area A between the voltage curve per unit period and the horizontal axis was obtained. Area B is the area when it is not attenuated. The voltage holding ratio is a percentage of the area A with respect to the area B.

Voltage holding ratio (VHR-2; 80 ° C; %): The TN device used for the measurement had a polyimide film, and the interval (cell gap) between the two glass substrates was 5 μm. The element is sealed after being placed in the sample as an adhesive which can be polymerized by ultraviolet light. A pulse voltage (5 V, 60 microseconds) was applied to the TN device to charge. The voltage of the attenuation was measured with a high-speed voltmeter at 16.7 msec, and the area A between the voltage curve per unit period and the horizontal axis was obtained. Area B is the area when it is not attenuated. The voltage holding ratio is a percentage of the area A with respect to the area B.

Voltage holding ratio (VHR-3; 25 ° C; %): After irradiating ultraviolet rays, the voltage holding ratio was measured, and the stability against ultraviolet rays was evaluated. The TN element used in the measurement had a polyimide film with a cell gap of 5 μm. A sample was injected into the element and irradiated with light for 20 minutes. The light source is an ultra-high pressure mercury lamp USH-500D (manufactured by Ushio Motor), and the distance between the component and the light source is 20 cm. In the measurement of VHR-3, the voltage of attenuation was measured at 16.7 msec. The composition having a large VHR-3 has great stability to ultraviolet rays. VHR-3 is preferably 90% or more, more preferably 95% or more.

Voltage holding ratio (VHR-4; 25 ° C; %): After the TN device in which the sample was injected was heated in a thermostat at 80 ° C for 500 hours, the voltage holding ratio was measured, and the stability against heat was evaluated. In the measurement of VHR-4, the voltage of the attenuation at 16.7 msec was measured. The composition having a large VHR-4 has great stability to heat.

Response time (τ; measured at 25 ° C; ms): An LCD5100 type luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. The light source is a halogen lamp. The low-pass filter is set to 5 kHz. The sample is placed in a normally black mode VA element in which the distance between the two glass substrates (cell gap) is 4 μm, and the rubbing direction is anti-parallel, and the adhesive is cured by an ultraviolet-curable adhesive. element. A rectangular wave (60 Hz, 10 V, 0.5 second) was applied to the element. At this time, the element was irradiated with light from the vertical direction, and the amount of light passing through the element was measured. When the amount of light is maximum, the transmittance is 100%, and when the amount of light is minimum, the transmittance is 0%. The response time is the time required for the penetration rate to change from 90% to 10% (fall time; fall time; milliseconds).

Specific resistance (ρ; measured at 25 ° C; Ω cm): 1.0 mL of a sample was injected into a container having an electrode. A DC voltage (10 V) was applied to the container, and a direct current of 10 seconds was measured. The specific resistance was calculated according to the following formula. (specific resistance) = {(voltage) × (capacitance of the container)} / {(direct current) × (dielectric constant of vacuum)}.

Gas Chromatography Analysis: A GC-14B gas chromatograph manufactured by Shimadzu Corporation was used for the measurement. The carrier gas was hydrazine (2 mL/min). The sample gasification chamber was set to 280 ° C and the detector (FID) was set to 300 ° C. A capillary column DB-1 manufactured by Agilent Technologies Inc. (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm; fixed liquid phase dimethyl polyoxane, non-polar) was used for the separation of the component compounds. ). The column was held at 200 ° C for 2 minutes and then heated to 280 ° C at a rate of 5 ° C / min. After the sample was prepared into an acetone solution (0.1 wt%), 1 μL of the sample was injected into the sample gasification chamber. The recorder uses the C-R5A type Chromatopac manufactured by Shimadzu Corporation or its equivalent. The obtained gas chromatogram shows the retention time and peak area of the peak corresponding to the component compound.

The solvent used to dilute the sample may also be chloroform or hexane. In order to separate the component compounds, the following capillary column can also be used. HP-1 (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm) manufactured by Agilent Technologies Inc., Rtx-1 manufactured by Restek Corporation (length 30 m, inner diameter 0.32 mm, film thickness) 0.25 μm), BP-1 manufactured by SGE International Pty. Ltd. (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm). In order to prevent the overlap of the peaks of the compounds, a capillary column CBP1-M50-025 (length 50 m, inner diameter 0.25 mm, film thickness 0.25 μm) manufactured by Shimadzu Corporation can also be used.

The ratio of the liquid crystalline compound contained in the composition can be calculated by the following method. The liquid crystalline compound can be detected by a gas chromatograph. The area ratio of the peaks in the gas chromatogram is equivalent to the ratio of the liquid crystal compound (molar number). When the capillary column as described above was used, the correction coefficient of each liquid crystal compound was regarded as 1. Therefore, the ratio (% by weight) of the liquid crystalline compound can be calculated from the area ratio of the peak.

The invention is illustrated in detail by way of examples. The invention is not limited by the following examples. The compounds in the comparative examples and examples are indicated by symbols based on the definitions of Table 3 below. In Table 3, the stereo configuration associated with 1,4-cyclohexylene is trans. In the examples, the numbers in parentheses after the mark correspond to the numbers of the preferred compounds. The symbol (-) indicates another liquid crystal compound. The ratio (percentage) of the liquid crystalline compound is a weight percentage (% by weight) based on the total weight of the liquid crystal composition, and other impurities are contained in the liquid crystal composition. Finally, the characteristic values of the composition are summarized.

[Comparative Example 1]

Composition No. 7 was selected from the compositions disclosed in the specification of International Publication No. 2009/034867. It is based on the fact that the composition contains the compound (1-1-1), the compound (3), the compound (3-4-1), the compound (4-1), the compound (4-1-2-1), and the compound. (4-1-4-1), and the absolute value of dielectric anisotropy is the largest. The composition and characteristics of the composition are as follows.

2-BBB(2F)-3 (1-1-1) 5%

3-HHB-3 (3-4-1) 5%

2-H2H-3 (3) 15%

3-H2H-V (3) 5%

3-H2B(2F,3F)-O2 (4-1-2-1) 20%

5-H2B(2F,3F)-O2 (4-1-2-1) 15%

3-HH2B(2F,3F)-O2 (4-1-4-1) 10%

5-HH2B(2F,3F)-O2 (4-1-4-1) 10%

5-BBEB(2F,3F)B-3 (4-1) 5%

5-HEB(2F,3F)HH-3 (4-1) 5%

5-BEB(2F,3F)HH-3 (4-1) 5%

NI = 84.9 ° C; Tc ≦ -20 ° C; Δn = 0.096; Δ ε = -3.5.

[Comparative Example 2]

Example 4 was selected from the compositions disclosed in Japanese Laid-Open Patent Publication No. 2009-035630.

It is based on the fact that the composition contains the compound (1-1-1), the compound (1-2-1), the compound (3-1-1), the compound (3-2-1), and the compound (3-3- 1), the compound (3-11-1), the compound (4-1-2-1), the compound (4-1-4-1), and the compound (4-1-5-1). The composition and characteristics of the composition are as follows.

2-BBB(2F)-3 (1-1-1) 3%

3-BB(3F,6F)B-2 (1-2-1) 3%

V2-BB(3F)B-1 (-) 3%

3-HH-V (3-1-1) 20%

3-HB-O2 (3-2-1) 5%

V2-BB-1 (3-3-1) 5%

5-HBB(3F)B-3 (3-11-1) 5%

3-H2B(2F,3F)-O2 (4-1-2-1) 9%

5-H2B(2F,3F)-O2 (4-1-2-1) 5%

3-HH2B(2F,3F)-O2 (4-1-4-1) 5%

2-HBB(2F,3F)-O2 (4-1-5-1) 5%

3-HBB(2F,3F)-O2 (4-1-5-1) 7%

3-Ch2B(2F,3F)-O2 (-) 5%

3-Ch1OB(2F,3F)-O2 (-) 5%

3-ChEB(2F,3F)-O2 (-) 5%

3-HChB(2F,3F)-O2 (-) 5%

3-HChEB(2F,3F)-O2 (-) 5%

NI = 78.9 ° C; Tc ≦ -20 ° C; Δn = 0.118; η = 17.5 mPa ‧; Δ ε = -2.9.

[Comparative Example 3]

Example 20 was selected from the compositions disclosed in Japanese Laid-Open Patent Publication No. 2008-088164.

It is based on the fact that the composition contains the compound (1-1-1), the compound (3-5-1), the compound (3-7-1), the compound (3-11-1), and the compound (4-1). And the absolute value of dielectric anisotropy is the largest. The composition and characteristics of the composition are as follows.

2-BBB(2F)-3 (1-1-1) 5%

2-BB(3F)B-3 (-) 5%

3-HBB-2 (3-5-1) 10%

3-HHEBH-5 (3-7-1) 7%

5-HBB(3F)B-2 (3-11-1) 5%

3-HB(2CL,3F)-O2 (4-1) 7%

5-HB(2CL,3F)-O2 (4-1) 7%

3-HBB(2CL,3F)-O2 (4-1) 7%

3-HHB(2CL,3F)-O2 (4-1) 5%

3-ChB(2F,3CL)-O2 (-) 10%

3-ChB(2CL,3F)-O2 (-) 10%

5-HChB(2F,3CL)-O2 (-) 7%

3-HChB(2CL,3F)-O2 (-) 5%

3-ChBB(2F,3CL)-O2 (-) 5%

5-ChBB(2CL,3F)-O2 (-) 5%

NI = 99.6 ° C; Δn = 0.136; η = 48.3 mPa ‧; Δ ε = -3.5.

[Comparative Example 4]

Example 13 was selected from the compositions disclosed in Japanese Laid-Open Patent Publication No. 2008-038109.

The composition is based on the compound (1-1-1), the compound (1-2-1), the compound (4-1-1-1), and the compound (4-1-3-1). The composition and characteristics of the composition are as follows.

2-BBB(2F)-5 (1-1-1) 4%

5-BBB(2F)-2 (1-1-1) 4%

2-BB(3F,6F)B-2 (1-2-1) 4%

2-BB(3F,6F)B-3 (1-2-1) 4%

3-HB(2F,3F)-O2 (4-1-1-1) 14%

5-HB(2F,3F)-O2 (4-1-1-1) 14%

3-HHB(2F,3F)-O2 (4-1-3-1) 11%

5-HHB(2F,3F)-O2 (4-1-3-1) 11%

2-HHB(2F,3F)-1 (4-1-3-1) 10%

3-HHB(2F,3F)-1 (4-1-3-1) 10%

3-HVdh-3 (-) 14%

NI = 84.8 ° C; Tc ≦ -30 ° C; Δn = 0.113; η = 30.2 mPa ‧ Δ ε = -3.6; Vth = 2.20 V.

[Comparative Example 5]

Example 17 was selected from the compositions disclosed in the International Publication No. 2007/108307.

It is based on the fact that the composition contains the compound (1-1-1), the compound (1-2-1), the compound (3-1-1), the compound (3-2-1), and the compound (4-1). Compound (4-1-6-1) and compound (4-1-7-1) with minimal viscosity. The composition and characteristics of the composition are as follows.

2-BBB(2F)-3 (1-1-1) 4%

2-BBB(2F)-5 (1-1-1) 3%

2-BB(3F,6F)B-2 (1-2-1) 3%

3-BB(3F,6F)B-3 (1-2-1) 3%

2-BB(3F)B-3 (-) 8%

3-HH-4 (3-1-1) 10%

3-HB-O2 (3-2-1) 5%

3-HHB(2F,3CL)-O2 (4-1-6-1) 5%

5-HHB(2F,3CL)-O2 (4-1-6-1) 5%

3-HB(2F,3CL)-O2 (4-1) 10%

5-HB(2F,3CL)-O2 (4-1) 10%

3-BB(2F,3CL)-O2 (4-1) 10%

3-HBB(2CL,3F)-O2 (4-1) 8%

3-HBB(2F,3CL)-O2 (4-1-7-1) 8%

5-HBB(2F,3CL)-O2 (4-1-7-1) 8%

NI = 81.8 ° C; Tc ≦ -20 ° C; Δn = 0.141; Δ ε = -3.1.

[Example 1]

2-BBB(2F)-3 (1-1-1) 3%

2-BBB(2F)-5 (1-1-1) 5%

5-BBB(2F)-2 (1-1-1) 6%

1-BBB(2F)-2V (1-1-1) 7%

3-BBB(2F)-2V (1-1-1) 5%

V2-BBB(2F)-1 (1-1-1) 3%

V2-BBB(2F)-2 (1-1-1) 3%

V2-BBB(2F)-3 (1-1-1) 3%

2-H1OB(2F,3F)-O2 (2-1-1) 5%

3-H1OB(2F,3F)-O2 (2-1-1) 5%

5-H1OB(2F,3F)-O2 (2-1-1) 8%

8-H1OB(2F,3F)-O2 (2-1-1) 5%

3-HH1OB(2F,3F)-O2 (2-5-1) 5%

3-HH1OB(2F,3F)-1 (2-5-1) 8%

3-HH1OB(2F,3F)-2 (2-5-1) 8%

5-DhH2B(2F,3F)-O2 (2-8-1) 8%

5-DhH1OB(2F,3F)-O2 (2-9-1) 8%

3-dhBB(2F,3F)-O2 (2-10-1) 5%

NI = 97.1 ° C; Tc ≦ -20 ° C; Δn = 0.155; η = 39.0 mPa ‧ Δ ε = -4.0; VHR-1 = 99.3%; VHR-2 = 98.2%; VHR-3 = 98.1%.

[Example 2]

2-BBB(2F)-3 (1-1-1) 5%

2-BBB(2F)-5 (1-1-1) 5%

5-BBB(2F)-2 (1-1-1) 5%

1-BBB(2F)-2V (1-1-1) 6%

3-BBB(2F)-2V (1-1-1) 7%

V2-BBB(2F)-1 (1-1-1) 7%

V2-BBB(2F)-2 (1-1-1) 5%

V2-BBB(2F)-3 (1-1-1) 5%

3-H1OB(2F,3F)-O2 (2-1-1) 10%

5-H1OB(2F,3F)-O2 (2-1-1) 10%

V-H1OB(2F,3F)-O2 (2-1-1) 8%

V-DhH1OB(2F,3F)-O2 (2-9-1) 6%

3-DhH1OB(2F,3F)-O2 (2-9-1) 8%

5-DhH1OB(2F,3F)-O2 (2-9-1) 8%

3-dhBB(2F,3F)-O2 (2-10-1) 5%

NI = 92.1 ° C; Tc ≦ -20 ° C; Δn = 0.171; η = 37.8 mPa ‧ Δ ε = -4.0; VHR-1 = 99.5%; VHR-2 = 98.5%; VHR-3 = 98.1%.

[Example 3]

2-BBB(2F)-3 (1-1-1) 5%

2-BBB(2F)-5 (1-1-1) 5%

5-BBB(2F)-2 (1-1-1) 7%

1-BBB(2F)-2V (1-1-1) 8%

V2-BBB(2F)-2 (1-1-1) 5%

V2-BBB(2F)-3 (1-1-1) 5%

5-BB(3F,6F)B-5 (1-2-1) 7%

5-BB(3F,6F)B-O6 (1-2-1) 7%

3-H1OB(2F,3F)-O2 (2-1-1) 8%

5-H1OB(2F,3F)-O2 (2-1-1) 10%

8-H1OB(2F,3F)-O2 (2-1-1) 10%

3-HH1OB(2F,3F)-O2 (2-5-1) 3%

5-HH1OB(2F,3F)-O2 (2-5-1) 7%

3-DhHB(2F,3F)-O2 (2-6-1) 5%

5-DhH1OB(2F,3F)-O2 (2-9-1) 8%

NI = 94.5 ° C; Tc ≦ -20 ° C; Δn = 0.169; η = 38.7 mPa ‧ Δ ε = -4.0; VHR-1 = 99.6%; VHR-2 = 98.1%; VHR-3 = 98.0%.

[Example 4]

2-BBB(2F)-3 (1-1-1) 5%

2-BBB(2F)-5 (1-1-1) 5%

5-BBB(2F)-2 (1-1-1) 7%

1-BBB(2F)-2V (1-1-1) 5%

1-BBB(2F)-2V1 (1-1-1) 7%

V2-BBB(2F)-2 (1-1-1) 4%

V2-BBB(2F)-3 (1-1-1) 4%

5-H1OB(2F,3F)-O2 (2-1-1) 8%

8-H1OB(2F,3F)-O2 (2-1-1) 8%

V-H1OB(2F,3F)-O2 (2-1-1) 7%

5-HH1OB(2F,3F)-O2 (2-5-1) 8%

1V2-HDhB(2F,3F)-O2 (2-7-1) 7%

3-DhH1OB(2F,3F)-O2 (2-9-1) 8%

5-DhH1OB(2F,3F)-O2 (2-9-1) 8%

3-HH-V (3-1-1) 5%

3-HH-V1 (3-1-1) 4%

NI = 96.7 ° C; Tc ≦ -20 ° C; Δn = 0.156; η = 34.8 mPa ‧ s; Δ ε = -4.0.

[Example 5]

2-BBB(2F)-3 (1-1-1) 3%

2-BBB(2F)-5 (1-1-1) 5%

1-BBB(2F)-2V (1-1-1) 5%

1-BBB(2F)-2V1 (1-1-1) 5%

V2-BBB(2F)-1 (1-1-1) 5%

V2-BBB(2F)-3 (1-1-1) 5%

3-H1OB(2F,3F)-O2 (2-1-1) 5%

5-H1OB(2F,3F)-O2 (2-1-1) 8%

8-H1OB(2F,3F)-O2 (2-1-1) 8%

V-H1OB(2F,3F)-O2 (2-1-1) 5%

3-Dh2B(2F,3F)-O4 (2-3-1) 5%

3-HH1OB(2F,3F)-O2 (2-5-1) 5%

5-HH1OB(2F,3F)-O2 (2-5-1) 3%

V2-HDhB(2F,3F)-O2 (2-7-1) 5%

3-dhBB(2F,3F)-O2 (2-10-1) 8%

5-dhBB(2F,3F)-O2 (2-10-1) 5%

3-HB-O2 (3-2-1) 5%

1V-HBB-2 (3-5-1) 7%

1O1-HBBH-4 (-) 3%

NI = 96.3 ° C; Tc ≦ -20 ° C; Δn = 0.160; η = 38.2 mPa ‧ Δ ε = -4.0.

[Example 6]

2-BBB(2F)-3 (1-1-1) 5%

2-BBB(2F)-5 (1-1-1) 5%

1-BBB(2F)-2V (1-1-1) 4%

3-BBB(2F)-2V (1-1-1) 5%

1-BB(3F,6F)B-2V (1-2-1) 5%

2-H1OB(2F,3F)-O2 (2-1-1) 6%

3-H1OB(2F,3F)-O2 (2-1-1) 6%

V-H1OB(2F,3F)-O2 (2-1-1) 5%

5-Dh2B(2F,3F)-O2 (2-3-1) 5%

3-HH1OB(2F,3F)-O3V (2-5-1) 5%

3-DhHB(2F,3F)-O2 (2-6-1) 3%

1V2-HDhB(2F,3F)-O2 (2-7-1) 5%

3-DhH1OB(2F,3F)-O2 (2-9-1) 5%

3-dhBB(2F,3F)-O2 (2-10-1) 8%

5-dhBB(2F,3F)-O2 (2-10-1) 8%

3-HB-O1 (3-2-1) 5%

V2-BB-1 (3-3-1) 5%

3-HHB-O1 (3-4-1) 5%

5-HBB(3F)B-3 (3-11-1) 5%

NI = 92.1 ° C; Tc ≦ -20 ° C; Δn = 0.155; η = 37.5 mPa ‧ s; Δ ε = -4.1.

[Example 7]

2-BBB(2F)-3 (1-1-1) 3%

2-BBB(2F)-5 (1-1-1) 3%

1-BBB(2F)-2V1 (1-1-1) 3%

V2-BBB(2F)-3 (1-1-1) 6%

2-H1OB(2F,3F)-O2 (2-1-1) 3%

3-H1OB(2F,3F)-O2 (2-1-1) 5%

V-H1OB(2F,3F)-O2 (2-1-1) 7%

1V2-HDhB(2F,3F)-O2 (2-7-1) 4%

V-DhH1OB(2F,3F)-O2 (2-9-1) 3%

3-DhH1OB(2F,3F)-O2 (2-9-1) 5%

3-dhBB(2F,3F)-O2 (2-10-1) 4%

5-dhBB(2F,3F)-O2 (2-10-1) 5%

3-HH-V (3-1-1) 8%

V2-BB-1 (3-3-1) 5%

1V-HBB-2 (3-5-1) 3%

3-HHEBH-3 (3-7-1) 3%

5-HBB(3F)B-3 (3-11-1) 3%

5-H2B(2F,3F)-O2 (4-1-2-1) 5%

5-HHB(2F,3F)-O2 (4-1-3-1) 5%

3-HBB(2F,3F)-O2 (4-1-5-1) 4%

1V2-HBB(2F,3F)-O2 (4-1-5-1) 5%

5-HHB(2F,3CL)-O2 (4-1-6-1) 3%

2-BB(2F,3F)B-4 (-) 5%

NI = 102.3 ° C; Tc ≦ -20 ° C; Δn = 0.151; η = 34.3 mPa ‧ s; Δ ε = -4.1.

[Example 8]

5-BB(3F,6F)B-5 (1-2-1) 10%

V2-BB(3F,6F)B-2V (1-2-1) 3%

V-H1OB(2F,3F)-O2 (2-1-1) 9%

3-HH1OB(2F,3F)-1 (2-5-1) 3%

1V2-HDhB(2F,3F)-O2 (2-7-1) 3%

5-DhH2B(2F,3F)-O2 (2-8-1) 3%

3-dhBB(2F,3F)-O2 (2-10-1) 10%

5-dhBB(2F,3F)-O2 (2-10-1) 10%

3-HB-O1 (3-2-1) 3%

V2-BB-1 (3-3-1) 10%

V-HHB-1 (3-4-1) 3%

1V-HBB-2 (3-5-1) 3%

3-HHEH-4 (3-6-1) 3%

3-HBBH-3 (3-8-1) 3%

V-HB(2F,3F)-O2 (4-1-1-1) 5%

3-HBB(2F,3F)-O2 (4-1-5-1) 6%

3-HBB(2F,3CL)-O2 (4-1-7-1) 3%

3-HH1OB(2F,3F,6Me)-O2 (4-1-9-1) 5%

2-BB(2F,3F)B-4 (-) 5%

NI = 93.7 ° C; Tc ≦ -20 ° C; Δn = 0.152; η = 37.9 mPa ‧ s; Δ ε = -4.0.

[Example 9]

2-BBB(2F)-3 (1-1-1) 5%

2-BBB(2F)-5 (1-1-1) 5%

5-BBB(2F)-2 (1-1-1) 4%

V2-BBB(2F)-1 (1-1-1) 3%

V2-BBB(2F)-3 (1-1-1) 7%

3-H1OB(2F,3F)-O2 (2-1-1) 7%

V-H1OB(2F,3F)-O2 (2-1-1) 8%

5-DhB(2F,3F)-O2 (2-2-1) 3%

5-Dh1OB(2F,3F)-O2 (2-4-1) 3%

3-dhBB(2F,3F)-O2 (2-10-1) 4%

5-dhBB(2F,3F)-O2 (2-10-1) 8%

5-HB-O2 (3-2-1) 3%

V2-BB-1 (3-3-1) 7%

3-HBB-2 (3-5-1) 5%

3-HHEBH-3 (3-7-1) 5%

5-HB(2F,3F)-O2 (4-1-1-1) 5%

1V2-HHB(2F,3F)-O2 (4-1-3-1) 3%

3-HBB(2F,3F)-O2 (4-1-5-1) 3%

1V2-HBB(2F,3F)-O2 (4-1-5-1) 3%

4O-Cro(7F,8F)H-3 (4-2) 3%

3-HH2Cro(7F,8F)-5 (4-2-3-1) 3%

3-HH1OCro(7F,8F)-5 (4-2-4-1) 3%

NI = 92.6 ° C; Tc ≦ -20 ° C; Δn = 0.155; η = 36.5 mPa ‧ s; Δ ε = -4.0.

[Example 10]

2-BBB(2F)-3 (1-1-1) 5%

5-BBB(2F)-2 (1-1-1) 4%

1-BBB(2F)-2V (1-1-1) 3%

3-BBB(2F)-2V (1-1-1) 5%

V2-BBB(2F)-3 (1-1-1) 6%

3-H1OB(2F,3F)-O2 (2-1-1) 10%

3-Dh2B(2F,3F)-O4 (2-3-1) 5%

5-DhH1OB(2F,3F)-O2 (2-9-1) 6%

3-dhBB(2F,3F)-O2 (2-10-1) 5%

5-dhBB(2F,3F)-O2 (2-10-1) 4%

V2-BB-1 (3-3-1) 9%

1V-HBB-2 (3-5-1) 4%

3-HB(3F)HH-5 (3-9-1) 3%

3-HB(3F)BH-3 (3-10-1) 3%

V-HB(2F,3F)-O2 (4-1-1-1) 3%

5-H2B(2F,3F)-O2 (4-1-2-1) 3%

5-HH2B(2F,3F)-O2 (4-1-4-1) 3%

5-HBB(2F,3F)-O2 (4-1-5-1) 6%

3-HH2B(2F,3F,6Me)-O2 (4-1-8-1) 4%

3-H2Cro(7F,8F)-5 (4-2-1-1) 3%

3-H1OCro(7F,8F)-5 (4-2-2-1) 3%

5-HB1OCro(7F,8F)-5 (4-2-5-1) 3%

NI = 93.2 ° C; Tc ≦ -20 ° C; Δn = 0.154; η = 38.3 mPa ‧ s; Δ ε = -3.9.

[Example 11]

2-BBB(2F)-3 (1-1-1) 7%

2-BBB(2F)-5 (1-1-1) 7%

5-BBB(2F)-2 (1-1-1) 5%

1-BBB(2F)-2V1 (1-1-1) 5%

V2-BBB(2F)-3 (1-1-1) 3%

3-HH1OB(2F,3F)-O2 (2-5-1) 10%

5-HH1OB(2F,3F)-O2 (2-5-1) 15%

3-dhBB(2F,3F)-O2 (2) 5%

2-HH-3 (3-1-1) 10%

3-HH-5 (3-1-1) 5%

V-HB(2F,3F)-O2 (4-1-1-1) 7%

2-HHB(2F,3F)-O2 (4-1-3-1) 11%

5-HHB(2F,3F)-O2 (4-1-3-1) 5%

2-BB(2F,3F)B-4 (-) 5%

NI = 113.7 ° C; Δn = 0.148; η = 29.0 mPa ‧; Δ ε = -3.8.

[Example 12]

2-BBB(2F)-3 (1-1-1) 7%

2-BBB(2F)-5 (1-1-1) 5%

5-BBB(2F)-2 (1-1-1) 5%

3-HH1OB(2F,3F)-O2 (2-5-1) 8%

3-HH1OB(2F,3F)-O3V (2-5-1) 12%

2-HH-3 (3-1-1) 15%

3-HH-5 (3-1-1) 5%

2-HHB(2F,3F)-O2 (4-1-3-1) 5%

2-HBB(2F,3F)-O2 (4-1-5-1) 10%

3-HBB(2F,3F)-O2 (4-1-5-1) 8%

5-HBB(2F,3F)-O2 (4-1-5-1) 8%

V-HBB(2F,3F)-O2 (4-1-5-1) 12%

NI = 115.7 ° C; Tc ≦ -20 ° C; Δn = 0.147; η = 31.2 mPa ‧; Δ ε = -4.1.

[Example 13]

2-BBB(2F)-5 (1-1-1) 5%

3-BBB(2F)-5 (1-1-1) 5%

5-BBB(2F)-2 (1-1-1) 5%

V2-BBB(2F)-3 (1-1-1) 3%

3-HH1OB(2F,3F)-O2 (2-5-1) 10%

5-HH1OB(2F,3F)-O2 (2-5-1) 10%

3-HB(2F,3F)-O2 (2-11-1) 5%

V-HB(2F,3F)-O2 (2-11-1) 5%

2-HHB(2F,3F)-O2 (2-13-1) 5%

3-HBB(2F,3F)-O2 (2-15-1) 7%

5-HBB(2F,3F)-O2 (2-15-1) 7%

1V2-HBB(2F,3F)-O2 (2-15-1) 5%

2-HH-3 (3-1-1) 7%

5-HB-O2 (3-2-1) 3%

V2-BB-1 (3-3-1) 6%

3-HHB-1 (3-4-1) 5%

3-dhBB(2F,3F)-O2 (2) 7%

NI = 110.9 ° C; Δn = 0.150; η = 29.6 mPa ‧; Δ ε = -4.1.

[Example 14]

2-BBB(2F)-3 (1-1-1) 5%

2-BBB(2F)-5 (1-1-1) 5%

3-BBB(2F)-5 (1-1-1) 5%

3-HH1OB(2F,3F)-O2 (2-5-1) 8%

5-HH1OB(2F,3F)-O2 (2-5-1) 8%

5-H2B(2F,3F)-O2 (2-12-1) 8%

5-HHB(2F,3F)-O2 (2-13-1) 5%

3-HBB(2F,3F)-O2 (2-15-1) 7%

5-HBB(2F,3F)-O2 (2-15-1) 7%

1V2-HBB(2F,3F)-O2 (2-15-1) 7%

2-HH-3 (3-1-1) 5%

3-HH-V (3-1-1) 5%

3-HB-O2 (3-2-1) 5%

V2-BB-1 (3-3-1) 5%

3-HHB-O1 (3-4-1) 5%

3-dhBB(2F,3F)-O2 (2) 5%

5-dhBB(2F,3F)-O2 (2) 5%

NI = 115.5 ° C; Tc ≦ -20 ° C; Δn = 0.148; η = 29.4 mPa ‧ Δ ε = -4.0.

The compositions of Examples 1 to 14 had a larger dielectric anisotropy and a larger optical anisotropy than Comparative Examples 1 to 5. Therefore, the liquid crystal composition of the present invention has characteristics superior to those of the liquid crystal compositions shown in Patent Documents 1 to 5.

[Industrial availability]

The liquid crystal composition of the present invention has a high temperature at the upper limit of the nematic phase, a low temperature at the lower limit of the nematic phase, a small viscosity, an appropriate optical anisotropy, a large negative dielectric anisotropy, a large specific resistance, and high stability against ultraviolet rays. At least one of the high thermal stability characteristics, or an appropriate balance between at least two characteristics. A liquid crystal display element containing such a composition is an AM element having a short response time, a large voltage holding ratio, a large contrast ratio, and a long life, and thus can be used in a liquid crystal projector, a liquid crystal television, or the like.

While the present invention has been described in its preferred embodiments, the present invention is not intended to limit the invention, and the present invention may be modified and modified without departing from the spirit and scope of the invention. The scope of protection is subject to the definition of the scope of the patent application.

Claims (14)

A liquid crystal composition having negative dielectric anisotropy and containing at least one selected from the group consisting of compounds represented by formula (1-1) and formula (1-2) as a first component a compound and at least one compound selected from the group consisting of compounds represented by formula (2-1) or formula (2-5) as a second component, the ratio of the first component is based on the total weight of the liquid crystal composition 5wt%~95wt% range, Here, R ¹ , R ² , R ³ and R ^{4 are} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyloxy group having 2 to 12 carbon atoms, and a carbon number. An alkenyl group having 2 to 12 alkenyl groups or an arbitrary hydrogen substituted with fluorine and having 2 to 12 carbon atoms. The liquid crystal composition according to claim 1, wherein the first component is at least one compound selected from the group consisting of compounds represented by formula (1-1). The liquid crystal composition according to claim 1, wherein the ratio of the first component is 10% by weight to 60% based on the total weight of the liquid crystal composition. The range of wt%, and the ratio of the second component is in the range of 10 wt% to 90 wt%. The liquid crystal composition according to claim 1, further comprising at least one compound selected from the group consisting of compounds represented by formula (3) as a third component, Here, R ⁵ and R ^{6 are} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or a carbon in which any hydrogen is replaced by fluorine. The number is 2 to 12 alkenyl; ring B, ring C and ring D are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or 3- Fluoro-1,4-phenylene; Z ² and Z ^{3 are} independently a single bond, an extended ethyl group, a methyleneoxy group, or a carbonyloxy group; p is 0, 1 or 2; when p is 1, the ring B, ring C and ring D are independently 1,4-cyclohexylene or 1,4-phenylene. The liquid crystal composition according to claim 4, wherein the third component is at least one compound selected from the group consisting of compounds represented by formula (3-1) to formula (3-11), Here, R ⁵ and R ^{6 are} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or a carbon in which any hydrogen is substituted by fluorine. The number is 2 to 12 alkenyl groups. The liquid crystal composition according to claim 4, wherein the ratio of the third component is 5 wt% to 60 based on the total weight of the liquid crystal composition. The range of wt%. The liquid crystal composition according to claim 1, further comprising at least one compound selected from the group consisting of compounds represented by formula (4-1) and formula (4-2) as a fourth component, Here, R ⁷ and R ^{8 are} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or a carbon in which any hydrogen is replaced by fluorine. The number is 2 to 12 alkenyl; ring E, ring F and ring G are independently 1,4-cyclohexylene or 1,4-phenyl; Z ⁴ is a single bond, an extended ethyl group, or a carbonyloxy group; Z ⁵ and Z ^{6 are} independently a single bond, an extended ethyl group, a methyleneoxy group, or a carbonyloxy group; X ⁴ and X ⁵ are fluorine or chlorine; Y ¹ is hydrogen or a methyl group; q is 1, 2 or 3 ;r and s are independently 0, 1, 2 or 3, and the sum of r and s is 3 or less. The liquid crystal composition according to claim 7, wherein the fourth component is selected from the group consisting of formula (4-1-1) to formula (4-1-9), and formula (4-2-1). At least one compound of the group of compounds represented by the formula (4-2-5), Here, R ⁷ and R ^{8 are} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or a carbon in which any hydrogen is replaced by fluorine. The number is 2 to 12 alkenyl groups. The liquid crystal composition according to claim 4, further comprising at least one compound selected from the group consisting of compounds represented by formula (4-1) and formula (4-2) as a fourth component, Here, R ⁷ and R ^{8 are} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or a carbon in which any hydrogen is replaced by fluorine. The number is 2 to 12 alkenyl; ring E, ring F and ring G are independently 1,4-cyclohexylene or 1,4-phenyl; Z ⁴ is a single bond, an extended ethyl group, or a carbonyloxy group; Z ⁵ and Z ^{6 are} independently a single bond, an extended ethyl group, a methyleneoxy group, or a carbonyloxy group; X ⁴ and X ⁵ are fluorine or chlorine; Y ¹ is hydrogen or a methyl group; q is 1, 2 or 3 ;r and s are independently 0, 1, 2 or 3, and the sum of r and s is 3 or less. The liquid crystal composition according to claim 9, wherein the fourth component is selected from the group consisting of formula (4-1-1) to formula (4-1-9), and formula (4-2-1). At least one compound of the group of compounds represented by the formula (4-2-5), Here, R ⁷ and R ^{8 are} independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or a carbon in which any hydrogen is replaced by fluorine. The number is 2 to 12 alkenyl groups. The liquid crystal composition according to claim 7, wherein the ratio of the fourth component is in the range of 5 wt% to 50 wt% based on the total weight of the liquid crystal composition. The liquid crystal composition according to claim 1, wherein the upper limit temperature of the nematic phase is 70 ° C or higher, and the optical anisotropy at a wavelength of 589 nm is 0.08 or more at 25 ° C, and is at a frequency of 1 kHz. The dielectric anisotropy is -2 or less at 25 °C. A liquid crystal display element containing the first item of the patent application scope The liquid crystal composition. The liquid crystal display device of claim 13, wherein the operation mode of the liquid crystal display device is a vertical alignment mode, a lateral electric field switching mode, or a polymer stable alignment mode, and the driving mode of the liquid crystal display element is an active matrix mode.